Established in 1565, St. Augustine is a paradise for history buffs and arguably the root the nation’s oldest city’s appeal as a popular destination. When my husband, Tim, and I mapped out (pun intended) our plan to visit all 50 states as a family by the time our son (now aged 9) graduates from high school, we decided to select cities to visit that would yield opportunities for what Tim calls “retention questions.” These are questions we would craft from interesting facts about each destination designed to help our kids remember key points about the places we explore. And as the oldest European settlement in America, St. Augustine proved to be a veritable treasure trove.

Castillo De San Marcos fort

Residing along the banks of the Matanzas River on the northeast coast of Florida, the charm of St. Augustine is found along its narrow cobblestone streets, the fabled Fountain of Youth, the stretch of white sand beaches of Anastasia Island (a protected wildlife sanctuary) and the coquina (unique locally quarried material comprised of small seashells) bastions of the Castillo De San Marcos fort. A relic of Spain’s early exploration of the Americas, this historic landmark bears the distinction of being the best-preserved Spanish colonial fort in the United States and the country’s only existing 17th century masonry military structure.

Completed in 1695, the formidable Castillo De San Marcos was besieged by English colonial forces in 1702. When they weren’t able to destroy the structure, British forces burned the then-surrounding city to the ground upon retreat, which is why no other building in St. Augustine today dates back to prior to that time. The site occupies about 20 acres and at night, the Castillo’s watchtowers are uplit from the moat below, giving the fortress a truly foreboding appearance from afar. Take a self-guided tour or schedule a tour with park rangers – expect to stay about 90 minutes to thoroughly explore the two floors, which include a chapel and single cell used as the city’s first jail, exhibits and grounds.

But we’re getting ahead of ourselves here … let’s start back at the beginning when in 1513 Ponce De Leon (a former shipmate of Christopher Columbus) became the first European man to set foot in what is now the mainland of the United States of America. It is said he came in search of an island with mysterious healing water. Whether he found it at the 15-acre plot of coastal property that is now home to the Fountain of Youth Archeological Park is up for debate, but the grounds today is a must-see attraction complete with a museum packed with authentic artifacts (including one of only two existing Jolly Rancher flags), a real working cannon (which they set off to our son’s delight at scheduled intervals) and of course the signature “fountain” from which you can sip a free sample of natural spring water that has been flowing here continuously since the native Timucuan Indians called this place home – thousands of years before the arrival of the Spaniards.

Starting at the Old City Gates and stretching for several picturesque blocks, St. George Street is the heart of St. Augustine’s Old Town (pedestrian-only except for some street crossings) lined with a series of old or re-created buildings in Spanish Colonial architectural style currently occupied by restaurants, boutiques, art galleries, specialty shops, souvenir stores and attractions including the evocative Colonial Spanish Quarter whe-re visitors can take an immersive journey through centuries of St. Augustine’s rich history, including its era as a 17th-Century Spanish fortified town. Our kids loved climbing the 35-foot watchtower and watching a military gunsmith repair all of the garrison’s weapons.

St. Augustine is also home to the Oldest Wooden School House, which dates back to sometime around 1716, was built from bald cypress and red cedar using wooden pins and iron spikes. Visitors can take a self-guided tour of classroom on the first floor (the second floor where the schoolmaster and his family would have lived is inaccessible to the public) or learn more about daily life at the schoolhouse via a robotic teacher and student.

Ripley’s Red Train Tour

The city’s original sightseeing tour, Ripley’s Red Train Tour (an 80 – 90, fully narrated tour that runs continuously from as early as 8:30 a.m. until 5 p.m.) allowed us to step off and re-board the open-air sightseeing train at our leisure – the train continually loops 7 miles and stops at dozens of historic sites. And a fun bonus is that Red Train riders can play Florida’s oldest mini-golf course (located at the City Marina) for only $1. The St. Augustine Municipal Marina is home to various sightseeing boat tours, including a narrated tour on the Scenic Cruise on the “Victory III” for a different perspective of this coastal city taken from its tranquil waters.

St. Augustine Pirate & Treasure Museum

Relive the Golden Age of Piracy at the St. Augustine Pirate & Treasure Museum where visitors are transported to the time of plundering pirates and swashbuckling adventures. This museum is home to the world’s largest collection of authentic pirate artifacts; fun, interactive exhibits like the spine-tingling Disney Imagineer-designed Below Deck sound experience of Blackbeard’s last battle; and one of only two existing 17th century Jolly Rogers.Destination dining

The Floridian

An artsy and inspired farm-to-table establishment, The Floridian (39 Cordova St.) features innovative Southern fare for “omnivores, herbivores and locavores” crafted from regionally-inspired and locally-sourced cuisine. Dishes here are a “synthesis of down-home Southern Comfort Foods and lighter, healthier, vibrant and creative dishes.” The Cornbread Stack is worth a special mention and arrives as a cheddar and veggie stuffed cornbread topped with a choice of blackened fish or tofu and served with sweet pickled veggies and chili-cumin aioli. Another popular pick was the Dixie Burger with all the fixings (options include pepper jack cheese, sautéed onions and roasted peppers).

Our family also thoroughly enjoyed the eclectic European and Asian fusion fare at the Gypsy Cab Company (828 Anastasia Blvd.) on nearby Anastasia Island just over the landmark Bridge of Lions. According to owner Pat Morrissey, the daily menu (or “cab fare”) is prepared by a creative culinary team who “borrow” from Italian, German, Cajun, Mediterranean, classical European, Asian, Southern and other “Floribbean” cuisines. Popular with the locals, this longstanding eatery serves up something for every palate – on the evening we visited, menu items included a flavorful “Gypsy Chicken,” braised lamb shank, a delicious blackened Mahi Mahi with Crab Florentine, Texas beef brisket and Eggplant Parmagiana.

Where to Stay

Ideally situated on Matanzas Bay within easy walking distance to bayfront restaurants, attractions and historic downtown, the Bayfront Marin House (bayfrontmarinhouse.com) is a luxury bed and breakfast inn offering its guests spectacular views of the water, full Southern breakfasts each morning (with entrees such as blueberry waffles, banana pancakes and bacon stratas) daily happy hour with homemade appetizers, sangria, wine and beer in the early evening, complimentary use of beach chairs and umbrellas and loaner bikes available for day trips. Originally built in the 1790s, the stately two-story home features wraparound porches, outdoor seating, a small gazebo and 15 individually styled rooms with private entrances – each named after a historical figure or location in town. Charming antique furnishings mix with modern amenities (free WiFi, smartphone docking station and flatscreen TVs).

But I have to say that the best part of our stay was the unparalleled level of personal service we enjoyed – owner Sandy couldn’t have been more accommodating in coordinating our reservation and her staff warm, friendly and highly attentive. Although every room was occupied, we felt as though we were the only guests on property.

Marmalade™ Magazine is a full color monthly magazine covering “all things kid” in Orange County, California. Our purpose and passion is to serve parents with fresh, fun, helpful and hopeful content that celebrates and inspires family life.